For starters, I still haven’t gotten cracking on
Pluggable Transports.
There’s been little time in my life to dig into it, but it’s still the
next big thing that has to happen. We recently updated the ports to
6.5.2, but didn’t make the cutoff date for the
OpenBSD 6.1 release. If you
install tor-browser on that version of OpenBSD by doing:

$ doas pkg_add tor-browser

you will get Tor Browser 6.5.

To rectify this situation I recently posted a patch to ports@ to
backport the 6.5.2 update to OpenBSD 6.1. Hopefully this will happen
sometime soon, so OpenBSD 6.1-stable users can have the latest Tor
Browser. I intend to carry on doing this as updates come out, since
pretty much every Tor Browser update can be considered a
critical/security update.

For what it’s worth, I highly recommend the
-stable update service provided by
M:Tier. M:Tier is run by OpenBSD developers
and does some really cool shit. I use the free service on my machine
at NYI via their
shell script.
When I have a few shekels I’ll pay for a subscription. I’ve asked
them and they said they are willing to produce updated packages for
Tor Browser ports on the -stable release. Perhaps
TDP can find a way to donate some HW or
otherwise support them.

If you run -current then
you can follow along as the ports are updated. This is how I use Tor
Browser.